Motor fuel



Patented Oct. 29, 1935 MOTOR FUEL Le Roy G. Story, Glenham, N. i,assignor to The Texas Company, New York, N. Y., a corporation ofDelaware No Drawing. Application December 8, 1933,

Serial No. 701,540

8 Claims.

This invention relates to motor fuels and more particularly to theprovision in a motor fuel, normally tending to form gum on storage, suchas cracked gasoline, of an antioxidant or gum inhibitor.

It is well known in the art that cracked gasolines or other motor fuelscontaining unstable unsaturated hydrocarbons are often adverselyaffected by light, heat or air and tend to depreciate in color andanti-knock properties and to form gum on standing. The present inventionhas for its object the production, from such unstable materials, of astabilized motor fuel containing an improved gum inhibitor.

The invention will be more fully understood from the followingdescription and examples thereof.

According to the invention there is provided in the motor fuel certainderivatives of fluorene, and specifically fluorene compounds containingat least one amino or hydroxy constituent, such as 1,2-diamino-fluorenewhich has the following structural formula:

9 H: c Hi It is possible, however, that one or moreamino or hydroxylgroups may be substituted at the nine various positions indicated.Usually the diamino, dihydroxy or aminohydroxy derivatives are the mostactive inhibitors. Among the useful compounds are included 1-amino-,2-amino-, 4-amino-, 9-amino-, 2,7-diamino-, 1,9-diamino-, 9,9- diamino-,2,9-diamino-, 3,6-diamino-, 9-hydroxy-, 2-hydroxy-, 3-hydroxy-,1,9-dihydrovy-, l-amino- 9-hydroxy-, 9-hydroxy-1-amino-,2-amino-9-hydroxy-, 2,3,7-triamino-9-hydroxy-fluorene.

Other compounds closely related to fluorene and containing the fluorenestructure are chrysofluorene and picene-fluorene which contain acondensed ring with a naphthalene nucleus instead of one or both of thebenzc :ie rings:

Ohryso'lluorene Picene-fluorene I The amino and hydroxy derivatives ofthe above compounds are useful as inhibitors and are included in theinvention.

Also contemplated within the scope of the invention are derivatives offluorenone, such as 2- amido-fluorenone having the following struc- 5tural formula:

The fluorene hydrocarbons are found in that fraction of coal tar boilingbetween about 270 and 300 C. which affords an available source of i5supply of raw materials for preparing the compounds useful for theinvention.'

The methods of preparation and the properties of the fluorene compoundsare described in the literature to which reference is made particular-20 1y to Beilstein, vol. XII, and Richter, vol. II. In general it may besaid that many of the amino and hydroxy compounds are readily preparedfrom the corresponding nitro and sulfonic acid derivatives by the usualprocedures of reduction and caustic fusion respectively.

In practicing the invention, about 0.005% to 0.1% by weight of one ormore of the inhibitors is incorporated into the gasoline to be treated.

It is preferable to add the inhibitor to the freshly distilled gasolineeither by dissolving the compounddirectly in the gasoline or with theaid of mutual solvents, such as acetone, benzol, etc.

As an example of the operation of the invention, there is dissolved in acracked gasoline showing about 100 mg. of gum per 100 cc. by the copperdish method (U. S. Bureau of Mines method 530.1) 0.01% by weight of1,2-diaminofluorene. The copper dish gum on the treated sample is about10 mg. per 100 cc. of the gasoline. Another sample of the gasolinetreated similarly y with 1,9-dihydroxy-fluorene gives substantially thesame results.

It is to be understood that I do not limit myself to compounds of thetype disclosed in which only amino or hydroxy substituents. are presentin the molecule. Obviously, many other substituents, such as alkyl,aryl, arylalkyl, halogen, etc., may be present in addition to the aminoand hydroxyl groups. In some cases it may be a distinct advantage tohave one or more of the above groups present in addition to the amino orhydroxyl radicals; for instance, such an auxiliary substituent adjacentto an active amino or hydroxyl radical often increases the activitythereof and enhances the general eifectiveness of the resulting compoundas an inhibitor.

This application is a continuation-in-part of my copending application,Serial No. 660,035, filed March 8, 1933.

Obviously many modifications and variations of the invention, ashereinbefore set forth, may be made without departing from the spiritand scope thereof, and therefore only such limitations should be imposedas are indicated in the appended claims.

I claim:

1. A low boiling cracked hydrocarbon distillate, normally tending todeteriorate and form gum on storage, and containing, in sufficientamount to substantially retard such deterioration and gum formation, acompound having the flourene structure and carrying a substituent of theclass of amino and hydroxyl groups in the 9 position.

2. A cracked hydrocarbon distillate of the class of gasoline andkerosene, normally tending to deteriorate and form gum on storage, towhich has been added in suflicient amount to substantially retard suchdeterioration and gum formation, a derivative of fiuorene containing oneor more substituents from the group consisting of amino and hydroxylradicals, at least one of said substituents being located in the 9position of th fiuorene nucleus.

3. A cracked hydrocarbon distillate of the class of gasoline andkerosene, normally tending to deteriorate and form gum on storage, andcontaining a polyhydroxy fiuorene in sufllcient amount to substantiallyretard such deterioration and gum formation, said polyhydroxy fiuorenecarrying a hydrmzyl group in the 9 position.

and hydroxyl groups, in sufllcient amount to substantially retard suchdeterioration and gum formation, said fiuorene compound carrying one ofsaid groups in the 9 position.

6. A cracked hydrocarbon distillate of the class of gasoline andkerosene, normally tending to deteriorate and form gum on storage, andcontaining 1,9-dihydroxy fiuorene in sufflcient amount to substantiallyretard such deterioration and gum :0

formation.

7. A cracked hydrocarbon distillate of the class of gasoline andkerosene, normally tending to deteriorate and form gum on storage, andcontaining 1,9-diamino fiuorene in sufllcient amount to substantiallyretard such deterioration and gum formation.

8. A cracked hydrocarbon distillate of the class of gasoline andkerosene, normally tending to de"- terlorate and form gum on storage,and containing l-amino-Q-hydroxy fiuorene in sufficient amount tosubstantially retard such deterioration and gum formation.

LE nor G. STORY. 3

